Outreach vs Yesware

Which one do AI engines recommend, and how do they differ on price, fit and features?

The short answer

Outreach is the stronger AI pick in Sales Engagement: it has a visibility score of 55.1 versus 1.8 for Yesware, and ranks ahead in 100% of the answers that name both.

Choose Outreach if…

You want the brand AI engines rank higher (55.1 vs 1.8)
You need ISO 27001 or ISO 27701 or ISO 42001 or HIPAA or CSA STAR coverage
You prefer a larger, established vendor (501–1,000 employees)
Enterprise-grade, mature task-driven sequencing platform

Choose Yesware if…

You want a free plan to start
AI answers describe it more positively (33% vs 28% positive)
Basic email tracking, templates, and campaigns inside Gmail or Outlook
Free-forever tier

AI visibility side by side

Latest weekly run · Nov 3

Metric	Outreach	Yesware
Visibility score	55.1%	1.8%
Change vs last week	down−20.3%	down−0.6%
Rank in Sales Engagement	#2	#33
Share of voice	10.1%	0.5%
Mentions this run	61	4
Positive in AI answers	28%	33%

The stronger value in each row is marked with a ✓.

Visibility score trend

Weekly runs over the last 60 days

Outreach −20.300000000000004pp · Yesware −0.5999999999999999pp over 1 weekly runs.

Engine by engine

Outreach leads on 3 of 3 engines

ChatGPT

58.9%

AI Mode

63%

Perplexity

43.5%

5.4%

OutreachYesware

Head to head in AI answers

2 engine answers name both brands

2Outreach ranked higher

0Yesware ranked higher

Prompt	Engine	Outreach	Yesware
What is the difference between a sales engagement platform and a CRM?	Perplexity	#3	#7
Which sales engagement platform offers a free trial?	Perplexity	#6	#11

Features, pricing & fit

Dimension	Outreach	Yesware
Pricing model	Per seat	Per seat
Entry price	Contact sales	Free; paid from $19 per seat / mo
Free plan	No	Yes
Deployment	—	Gmail Chrome extension and Outlook add-in, cloud-hosted on Amazon Web Services and Heroku
Compliance	SOC 2 Type II, ISO 27001, ISO 27701, ISO 42001, HIPAA, CSA STAR	SOC 2 Type II
Support	Plus support included with Amplify Core, Managed services included with Amplify Pro, Technical account management and enterprise support, Professional services packages for onboarding	Email support, Phone support on Pro and above, Help Center, Weekly webinar trainings
Founded	2014	2010
Headquarters	Seattle, Washington	Saskatoon, SK, Canada
Employees	501–1,000	51–200
Funding	Series G · $489M raised	Funding round · $48M raised
Best for	Revenue teams, from SDRs and account executives to sales managers, RevOps and customer success, that want prospecting, deal management, coaching and forecasting in one platform.	Individual sellers, sales teams and SMBs that sell through email and want simple tools without enterprise overhead